CEO First-Year Roadmap
Partner with us to make the most of your first year in your new nonprofit leadership role.
You’re a new nonprofit CEO, or at least new at your current organization. You want to hit the ground running, make the right impression, build the right relationships, and tackle the right things first. But there’s a lot you’re still learning, and some of what you don’t know yet could matter.
You want to get in quickly, but you also need to take the time to meet your Board of Directors and get to know your staff. You need to assess the landscape and determine what you need to do in your first year to move the needle on your mission.
That’s where Prosper comes in, ready to expedite your onboarding, act as your strategic sounding board, and partner with you every step of the way as you master your new role.
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How the CEO First-Year Roadmap Works
The CEO First-Year Roadmap is designed to help you step into leadership with clarity, focus, and an outside strategic partner who can help you make sense of what you are learning. We start with a diagnostic, translate that insight into a one-year roadmap, and then stay with you as a sounding board and accountability partner throughout your first year.
Your Nonprofit's Diagnostic
Our CEO First-Year Roadmap starts with a one-month diagnostic designed to help you hit the ground running with clarity. While Prosper assesses your organization's current state, including financial health, structure, board dynamics, and landscape, you are out in the field meeting with your board, staff, and funders.
We collaborate with you to develop the questions to ask, debrief with you afterward, and help you think through what it all means.
Your State of the Organization
At the end of month one, Prosper delivers a State of the Organization, a concise diagnostic of where your organization stands and a prioritized view of where you need to focus first.
Half-Day Roadmap Planning Session
Next, we spend a half day together translating your State of the Organization into three to five priorities for the year ahead, along with the specific, measurable objectives that will guide your leadership going forward.
Monthly Strategy Sessions
After the first three months, you have clarity and focus about what the rest of the year looks like, and a roadmap to share with your board. Over the remaining nine months, we meet with you each month to track progress, work through issues that come up, and help you navigate the inevitable challenges that arise as an impartial, outside sounding board.
Your First-Year Roadmap, Month by Month
Here is a breakdown of the CEO First-Year Roadmap by month, from diagnostic through ongoing strategy support.
Diagnostic
Prosper conducts an organizational assessment covering financial health, board dynamics, and organizational structure, plus a landscape overview of your subsector. At the same time, you are in the field meeting with board members, leadership staff, and key funders using question guides we collaborate with you to develop. We close the month with a debrief session to synthesize what you have learned.
State of the Organization
Prosper delivers a concise snapshot of where your organization stands, its strengths, its gaps, and what is ahead for you as a leader. You will share this with your board chair, leadership team, and with the full board as appropriate, as a foundation for what comes next.
Half-Day Roadmap Session
We spend a half day together translating your State of the Organization into a one-year plan: three to five priorities and the specific, measurable objectives that will guide your first year of leadership.
Monthly Strategy Sessions/h3>
Each month, we meet to track your progress against the roadmap, work through challenges, and keep you moving forward. Think of us as your strategic sounding board, accountability partner, and expert advisor on whatever comes your way.
The CEO First-Year Roadmap is a 12-month engagement.
Investment can be paid in installments. This includes the first-month diagnostic, State of the Organization, half-day roadmap planning session, and monthly strategy sessions for the remainder of the year.
Get StartedLet’s partner on your success
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Frequently Asked Questions
Is this right for a CEO who is brand new to the nonprofit sector, or only for someone new to a specific organization?
This is for any nonprofit CEO who is new to their role, whether you are coming from another nonprofit or stepping into the sector for the first time. For those new to the sector, we will cover the nuances that are unique to nonprofit leadership, including how to navigate the CEO and board relationship, how to read your organization's financial health through a nonprofit lens, and what “good” looks like in this context.
When is the right time to engage Prosper, before day one or once I am already in the role?
We have CEOs who engage us before they even begin, so we are ready to go on day one. More often than not, CEOs come to us within their first few weeks or months of a new role.
I am not in my first year. Can I still work with you to build a roadmap?
Yes. We can meet you where you are and adapt the roadmap to your current tenure.
How does the CEO First-Year Roadmap differ from executive coaching?
Executive coaching focuses on you and your skills as a leader, which could translate to any leadership role. The CEO First-Year Roadmap focuses on you and your organization.
We bring proprietary research and diagnostic tools to give you a clear picture of where your organization stands, then work alongside you to translate that into a concrete plan. You leave with deliverables, including a State of the Organization and a strategic roadmap, not just insight.
Who else at the organization is involved?
This engagement is one-on-one with the CEO or executive director. That said, we help you navigate dynamics with your board chair throughout, and there may be occasions where we include them in a meeting or two.
Can we keep sensitive information about the board and staff confidential?
Yes, absolutely. What you share with Prosper stays with Prosper.
Will you send us a proposal?
This page is our proposal. If you are ready to get started or have questions, reach out and we will take it from there.
Ready to start navigating your first year as a CEO together?
We can help you make the most of your first 12 months in your new role.
Schedule a Discovery Call